Calculation of 13C NMR chemical shifts and coupling constants for the analysis of conformer populations and relative configuration in flexible molecules

Molecular Physics

Volumn 92, Issue 3, 1997, Pages 569-580

  Stahl, Martin ^a   Schopfer, U ^a   Hoffmann, G F R W ^a  

^a Laboratory for Surface Studies   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000869612     PISSN: 00268976     EISSN: 13623028     Source Type: Journal    
DOI: 10.1080/002689797170310     Document Type: Article

References (40)

1. Pople, J., 1958. Molec. Phys., 1:3
2. Kalinowski, H.-O., Berger, S., and Braun, S., 1988. Carbon-13 NMR Spectroscopy, Chichester:Wiley. Pihlaja, K., and Kleinpeter, E., 1994, Carbon-13 NMR Chemical Shifts in Structural and Stereochemical Analysis (Weinheim:VCH)
3. Fäcke, T., and Berger, S., 1995. J. Amer., chem. Soc., 117:9547
4. Kozminski, W., and Nanz, D., 1966. J. magn. Reson., A, 122:245
5. Kozminski, W., Sperandio, D., and Nanz, D., 1966. Magn. Reson. Chem., 34:311
6. Gauss, J., 1995. Ber. Bunsenges. phys. Chem., 99:1001
7. Rauhut, G., Puyear, S., Wolinski, K., and Pulay, P., 1966. J. phys. Chem., 100:6310
8. Stahl, M., Schopfer, U., Frenking, G., and Hoffman, R. W., 1966. J. org. Chem., 61:8083
9. Stahl, M., and Schopfer, U., 1997. J. chem. Soc. Perkin Trans., 2 in press
10. Stahl, M., Schopfer, U., Frenking, G., and Hoffmann, R. W., 1997. J. org. Chem., 62:3702
11. Hoffmann, R. W., 1992. Angew. Chem., 104:1147 Angew. Chem. Int. Edn Engl., 31, 1697
12. Goto, H., Osawa, E., and Yamato, M., 1993. Tetrahedron, 49:387
13. Chang, G., Guida, W. C., and Still, W. C., 1989. J. Amer. chem. Soc., 111:4379
14. Macromodel 4.5, New York:Department of Chemistry, Columbia University. NY 10027
15. Allinger, N. L., Yuh, Y. H., and Lii, J.-H., 1989. J. Amer. chem. Soc., 111:8551 the 1994 version can be obtained from QCPE
16. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Gill, P. M. W., Johnson, B. G., Robb, M. A., Cheeseman, J. R., Keith, T. A., Petersson, G. A., Montgomery, J. A., Raghavachari, K., Al-Laham, M. A., Zakrzewski, V. G., Ortiz, J. V., Foresman, J. B., Cioslowski, J., Stefanov, B. B., Nanayakkara, A., Challacombe, M., Peng, C. Y., Ayala, P. Y., Chen, W., Wong, M. W., Andres, J. L., Replogle, E. S., Gomperts, R., Martin, R. L., Fox, D. J., Binkley, J. S., Defrees, D. J., Baker, J., Stewart, J. P., Head-Gordon, M., Gonzalez, C., and Pople, J. A., 1995. Gaussian 94 Revision A.1, Pittsburg, PA:Gaussian, Inc.
17. Lii, J.-H., and Allinger, N. L., 1994. J. phys. org. Chem., 7:591
18. Malkin, V. G., Malkina, O. L., and Salahub, D. R., 1993. Chem. Phys. Lett., 204:8087 Malkin V. G., Malkina, O. L., Casida, M. E., and Salahub, D. R., 1994, J. Amer. chem. Soc., 116, 5898
19. Malkin, V. G., Malkina, O. L., and Salahub, D. R., 1994. Chem. Phys. Lett., 221:91
20. St.-Amant, A., and Salahub, D. R., 1990. Chem. Phys. Lett., 169:387 Salahub, D. R., Fournier, R., Mlynarski, Papai, I., St.-Amant, A., and Ushio, J., 1992, Density Functional Methods in Chemistry, edited by J. Labanowski and J. Andzelm (New York:Springer) p. 77:Godbout, M., Salahub, D. J., Andzelm, J., and Wimmer, E., 1992, Can. J. Chem., 70, 560
21. Perdew, J. P., 1986. Phys. Rev. B, 33:8822 34, 7406
22. Perdew, J. P., and Wang, Y., 1992. Phys. Rev. B, 45:13244 Perdew, J. P., Chevary, J. A., Vosko, H., Jackson, K. A., Pederson, M. R., Singht, D. J., and Fiolhais, C., 1992, Phys. Rev. B, 46, 6671
23. Kutzelnigg, W., Fleischer, U., and Schindler, M., 1990. NMR—Basic Principles and Progress, Vol. 23, 165Heidelberg:Springer.
24. Beierbeck, H., and Saunders, J. K., 1980. Can. J. Chem., 58:1258 Gonzalez-Sierra, M., Bustos, D. A., and Ruvedo, E. A., 1987, Can. J. Chem., 71, 71
25. Whitesell, J. K., La Cour, T., Lovell, R. L., Pojman, J., Ryan, P., and Yamada-Nosaka, A., 1988. J. Amer. chem. Soc., 110:991
26. It has been suggested that an increment system based on IGLO-calculated NMR shifts could be constructed for hydrocarbons:Schindler, M., and Kutz elnigg, W., 1983, J. Amer. chem Soc., 105, 1360.
27. Kim, J.-C., Lee, Y.-W., Tamura, H., and Yoshizawa, T., 1995. Tetrahedron, 36:1047
28. Biskupiak, J. E., and Ireland, C. M., 1983. Tetrahedron Lett., 24:3055
29. Oppolzer, W., Moretti, R., and Bernardinelli, G., 1986. Tetrahedron Lett., 27:4713
30. Garson, M. J., Small, C. J., Skelton, B. W., Thinapong, P., and White, A. H., 1990. J. chem. Soc. Perkin Trans. 1,:805
31. Sugawara, K., Toda, S., Moriyama, T., Konishi, M., and Oki, T., 1993. J. Antibiotics, 46:928
32. Devys, M., Féréz ou, J.-P., Topgi, R. S., Barbier, M., Bosquet, J.-F., and Kollmann, A., 1984. J. chem. Soc. Perkin Trans 1,:2133 Hassan, H. A. M., and Tamm, C., 1996, Helv. chim. Acta, 79, 518 and references therein
33. Abiko, A., and Masamune, S., 1996. Tetrahedron Lett., 37:1081
34. Hobza, P., Mulder, F., and Sandorfy, C., 1981. J. Amer. chem. Soc., 103:1360 Bacon, J. F., and van der Maas, J., 1988, J. chem. Soc. Perkin Trans 2, 1805
35. Uzawa, J., Zushi, S., Fukuda, Y., Nishihata, K., Umemura, K., Nishio, M., and Hirota, M., 1980. Bull. chem. Soc. Jap., 53:3623
36. Haasnoot, C. A. G., de Leeuw, F. A. A. M., and Altona, C., 1980. Tetrahedron, 36:2783
37. Berger, S., 1980. Org. magn. Res., 14:65
38. Krivdin, L. B., and Della, E. W., 1992. Progr. nucl. magn. Reson. Spectrosc., 14:301
39. Barfield, M., 1980. J. Amer. chem. Soc., 102:7
40. Gung, B. W., Zhu, Z., and Fouch, R., 1995. J. Amer. chem. Soc., 117:1783